


THE CHALLENGE

by MarmeLady_Orange



Category: Supernatural
Genre: Alternate Universe- No Supernatural, Bi-Curious Dean Winchester (even though he didn't know it), Dean Winchester Being an Idiot, Dean Winchester's First Time With a Man, Dean dates Castiel for a challenge, First Date, I have trouble finding tags for this, It's like they're in a teen drama, M/M, Or... Friends meet She's All That, Power Bottom Castiel (Supernatural), Re-imagining of an already existing piece of fiction (see the notes), Smooth Castiel (Supernatural), Something to that effect!, Sorry for the sucky tags!!!, Think The Office meets She's All That, but they're adults, dinner and a movie
Language: English
Status: Completed
Published: 2019-06-04
Updated: 2019-06-04
Packaged: 2020-04-07 10:51:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 9,112
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19083544
Author URL: https://archiveofourown.org/users/MarmeLady_Orange/pseuds/MarmeLady_Orange
Summary: Dean Winchester loves women, and women love him. Except there's a rumor going around at the office that he's dating Castiel Novak. Which, according to Kali, is ridiculous because Dean is way out of Castiel's league. His ego wounded, Dean vows Castiel will soon be eating in the palm of his hand. It doesn't go exactly as planned.Bonus: You get to choose between two endings!





	1. THE STORY

**Author's Note:**

> First of all... this story isn't mine, not really. This was the plot for an episode of that show I used to watch. And unless you are French Canadian, I don't think you would have seen it. (For you québécois out there, it's from C.A., S1 Ep.5, Le Coming In)
> 
> I'm not sure when this was done, early 2000s I think. And even though the base plot isn't mine, I had to adapt the storyline a whole lot, mostly to change one particular character. He didn't really take it well that his best friend would have been into dudes all of a sudden. I didn't want that in my story, so I changed the best friend for an understanding brother. ;)
> 
> Anyway... since most of you probably won't even know what I'm talking about, it's all new, I guess. lol
> 
> I know, Dean is being a dumb-dumb in this story. It's totally on purpose, seeing where the plot comes from was a comedy... a dramedy... drama and comedy... anyway! A bit of funny, a bit of feels.
> 
> That being said, there's one important thing you need to know. I wrote two endings (the chapter names indicate which is which). I mean, you can read both, but if you only want to read the happy ending, you can also do that. Or you could decide that the "real" ending is what you want. It's up to you!
> 
> From the moment I decided to write this (a loooong time ago), I knew I had to have a Destiel ending. Even if the show hadn't done that (the whole thing was mostly a lesson for the serial-dating character, you'll see why if you read that not happy ending).
> 
> So there you go... One story, two endings.

Why Mr. Adler thought Monday mornings were the best time for staff meetings, Dean would never know. Not only had everyone pretty much forgotten what happened the week before, but some were also still, maybe, kind of drunk from partying all weekend.

And by some, Dean knew he probably was the only one doing that. Everybody else was too responsible, or boring, or married, or—

“—why Dean Winchester would be the best one here to penetrate this particular market.”

Hearing his name was enough to startle Dean into paying attention again. He looked up to see Mr. Adler looking at him expectantly. Had he asked a question? Dean looked around to see everyone also waiting for him to say something. He smirked.

“My strategy would be to penetrate that market through the back door. I’m told it can be quite surprising when unexpected.”

Of course, his quip didn’t get anything other than eye rolls and huffs. He had to bite the inside of his cheek to keep his laughter at bay. Would his friends have been here, they would have laughed, no doubt about it. Where were they when he needed their humorous support?

“On such a high note, I guess the meeting is over,” Mr. Adler said, his tone a little defeated. “I just want to remind you that in three weeks, it’s the official Sandover Summer Slam at our beloved CEO’s home in the Hamptons.”

A couple of excited yesses were let out.

“Also, a reminder that you can bring your spouses.”

This time, Mr. Adler’s words were met with sighs and whines. “But you don’t have to,” he added, winking at nobody in particular. Chuckles answered him as people started making their way out of the boardroom. Before he could leave, Dean found his boss coming to stand in his way.

He swallowed, kind of worried he was about to get scolded. He didn’t really know what it would be for, but he imagined Zach had plenty of reasons anyway. He swallowed again when Zach entered his personal space to speak, his voice low.

“You know, if you want to bring Castiel along, nobody will mind.”

Dean couldn’t swallow this time, his jaw slack. Castiel? Novak? The new dude from accounting?

“What?”

“We’re very open here at Sandover, Dean. We don’t mind one bit that you and Castiel are being homosexual together.” The smile on Mr. Adler’s face widened, but it didn’t reach his eyes. “I mean, we certainly can appreciate how discreet you both are. If you want to come together to the party, it’s more than all right.”

As if worried that Dean wouldn’t believe him, Zach grabbed his shoulder and squeezed it, still smiling with that weird look in his eyes. Yeah… even if he was gay, there was no way he could ever think it would be okay to bring his boyfriend to an office party.

Except he wasn’t gay. Before he could even try to deny or ask questions, Mr. Adler was leaving the boardroom, leaving a bewildered Dean behind.

He took his time going back, making a pitstop in the kitchenette to grab a coffee, then swerving to see Kali instead of going to his own office.

“Adler thinks I’m gay,” he said without preamble as he came to stand in front of her desk. She quirked an eyebrow and smirked as she closed the lid of her computer.

“What makes you say that?”

“He told me I could go to the party in the Hamptons with Castiel. Like… with him! What the hell, Kali? Why would he even think that? He’s known me for years and… I get why Zach would think that Novak’s a—you know—but me?”

Kali shrugged, not looking all that shocked by the news. “It’s not like he’s the only one thinking it.” She sighed, then shrugged again. “I don’t really get it, to be honest. I mean… the guy’s a dreamboat.”

“Novak? A dreamboat?” Dean said in a scoff. “You better not be saying that he’s outta my league. Are you?”

“Out of your league? Honey, you’re not even on the same scale. I mean, you’re super cute and all, but… he’s legit handsome. And so chic, and cultured, you know?”

“I’m cultured, I know stuff. And I’m handsome, too. Believe me, Novak would be lucky that I even looked at him.”

Kali chuckled, shaking her head. “When’s the last time you even saw a play, Dean? Do you know any music that’s not from the ’70s? Any good restaurant you went to lately?”

“You don’t have to be a snob to be cultured, I’ll have you know.” He batted a hand in the air, pacing around the small office now. “I like what I like ‘cause it’s good, and it’s fun.” He stopped to point a finder at Kali. “You just wait. Before you know it, I’ll have Novak eating in the palm of my hand.”

~ • ~

“So what? You’re gay now?”

Dean rolled his eyes, chuckling. “No, Jo… what I am is a winner! And I’m gonna win that bet!”

“You made a bet about seducing some poor dude who’s never done anything to you? Could you be any more teen drama?” Charlie said, not sounding all that impressed. “How much?”

“Well, it’s not really a bet, there’s no money involved. It’s more like a personal challenge.”

“A challenge? Making this dude think you’re into him? What’s wrong with you, Dean? When did you become a bully?”

“Charlie…”

“I don’t wanna hear it!”

Before Dean could try and explain himself, Charlie stormed out on the terrasse, slamming the sliding door shut on her way out.

“She’s right, you know,” Sam said. “That’s a very mean prank to pull on someone. And pretty childish.”

“It’s not a prank.” Dean cleared his throat, crossing his arms over his chest as if to stave off the attacks coming at him from all sides. “Kali said the guy was out of my league, Sammy. I just wanna prove to her that she’s wrong.”

“And that makes it all right?”

“It’s not like I’m gonna go and ask the guy to marry me or something. I just want him to wanna date me. And then Kali will see I’m worth a date if this guy wants me.”

“So it’s all about Kali?” Jo asked, her mouth in a quirk. “Why don’t you just ask her out?”

“He’s tried that. Lots,” Sam said, chuckling. “She wants nothing to do with him.”

Dean scoffed, leaning back to chug on his beer while Jo and Sam laughed. They were still chuckling when Charlie came back in to stand in front of Dean.

“I’m not happy with you,” she said, arms crossed over her chest. “I forbid you to go forward with that stupid plan of yours.”

“Like I was telling those two clowns, I don’t wanna ask the guy to marry me. I just want him to wanna date me. I’ll make sure he asks me on a date, turn him down super gently and shit, and that’ll be that. Nobody’s gonna get hurt.”

“What if you’re wrong? What if he actually comes to like you? What then?”

“What if you’re the one who falls for him?”

Charlie’s questions were easy to ignore in the face of Sam’s own line of questioning.

“What? Sam, no! No way I’m falling for the guy… I mean… he’s a guy!”

“So?”

His two best friends and his brother were looking at him, expectant. They really were waiting for an answer. As if they didn’t know already.

“So? So I don’t like guys that way.”

“How do you know?” Charlie asked.

He huffed. “The same way you know you don’t like ’em either, Charlie. I like girls… I mean, I love girls. Aren’t you guys always lecturing me about liking girls a little too much?”

“He makes a point,” Jo said, clinking her bottle with Dean’s. “Although trying out stuff doesn’t hurt either. Just sayin’,” she added, challenging Charlie’s raised eyebrow with a pointed look. “Not talking about this now. Remember? Dean wants to date a dude?”

“I don’t! You know what? Forget I said anything, all right?” Dean said, making Jo and Sam laugh again.

“Are you really gonna go through with your stupid plan?” Charlie asked, not backing down. When Dean didn’t answer or looked at her, she shook her head. “This whole thing is gonna turn to shit, Dean. And when it does, you better not come and whine to me about it. Because all I’ll have to answer is that I told you so.”

~ • ~

The next morning, Dean hadn’t changed his mind. Unlike he usually did, he kept his office door open, hoping to catch Castiel on his way to the kitchenette. He had to wait until around three in the afternoon before the accountant came out of hiding.

The second he walked past, Dean was up and following him, hoping he was actually going to the kitchen and not the bathroom. Because that would have been weird.

“Hey… Castiel, right?” Dean said when he entered the kitchenette after him.

He must have been in his own mind because Dean’s voice seemed to startle him and he turned around, looking a bit spooked. The first thing Dean noticed was how blue his eyes were. Had they always been this blue? Was he wearing contacts?

Dean put his hands up, placating. “Hey, sorry… didn’t wanna scare you. Just wanted to say hi!”

Castiel was squinting now, his head slightly tilted. “Hello?” he said, obviously confused. “And you are Mr. Winchester, right?”

“Mr. Winchester was my father… I’m Dean,” he said. His voice was mellow, and he came to stand a bit too close as he offered his hand to shake. As Castiel took it, Dean let his gaze travel over Castiel’s concealed form. That suit was atrocious, how could Kali think this guy was hot?

“How is it that we’ve never met?” Dean asked when he took his hand back. “You’ve been working here for what… six? Seven months?”

“Fourteen months, actually.”

“Really? How come you weren’t at the last Christmas party?”

This time, something seemed to click in Castiel. He straightened up, a single corner of his mouth quirking up. He took a step into Dean’s personal space to speak, his voice low and rough. “Maybe you were too busy trying to fuck Kali Sharma to notice me.”

“I wasn’t—I—what?” Dean cleared his throat. “I mean—did you see her? Who wouldn’t try to get with that?” he said as he tried to find his footing again.

Castiel smirked and turned around to use the coffee maker. Dean waited while he took his time picking a pod, then fed it to the machine. While his tea was brewing, he turned back around, still with that smirk on his face.

“I wouldn’t want to ‘get with that’,” he said, finger quotes included. “I’m gay, but you know that, don’t you?”

The lump in Dean’s throat was too thick for him to answer, so he just nodded as he tried to swallow it down. Castiel’s smiles softened a bit as he picked lint from Dean’s jacket.

“How long have you known?”

Dean needed to clear his throat again. “Huh—that you’re—huh—gay?”

“No. That you like boys.” Castiel’s voice was soft and low, and Dean wasn’t sure he liked what it did to him.

He licked his lips, his instincts urging him to tell Castiel he didn’t like guys, but he fought through it, even managing to give him a smile back.

“Always known, I guess,” he mustered to say, his voice a little shaky. “You’re cute,” he added, feeling the tip of his ears grow warm. And before he could stop himself, this little gem fell from his mouth: “So… wanna go grab a drink or something?”

Shit! That wasn’t the plan. Dean was supposed to make sure the guy would ask him out so he could turn him down. There was no winning here because whatever Castiel answered, Dean was screwed. Either he would have to go on a date with him, or he would have to live with the fact that this supposedly hot dude didn’t want him.

“I don’t think Mr. Adler would appreciate us going for a drink right now,” Castiel answered, deadpan. “Plus, I’m not really a getting-drinks kind of man.”

Dean’s stomach dropped, already dreading having to face Kali when she would learn about him being rejected by prissy Novak.

“I wouldn’t be against going on a date, though. If that’s something you’d like to do, of course.”

There it was, the overture Dean had needed. He had found the best way to let him down, too. Had rehearsed it in his mind numerous times. All he had to do was smile, gently pat him on the shoulder and say that he was sorry, that he really just wanted to chat, not date. What he said instead was a trembling, “Okay.”.

Castiel leaned in to brush his lips against Dean’s cheek, making him bristle. “Is Friday good for you?” he said as he leaned back. “We could go grab some food and go to your place? A nice dinner, some Netflix, then see where the evening takes us?”

Dean could only nod, his mind right about to shut down.

“Let’s meet in the parking lot at five Friday, then,” Castiel said before kissing his cheek again and leaving him alone in the kitchenette.

~ • ~

“So… Sammy? Do you have plans tomorrow night?”

Dean knew it was kind of a shitty thing to wait until the day before to ask his brother to find somewhere else to be because he had a date, but doing this any earlier would have meant he would be getting the third degree for much longer. Like this, he would only be getting it until either one went to bed. And Dean wasn’t intending on doing that too late either.

“Supposed to go to the movies with Jessica. Why?”

“Could you maybe not come back here after the movie? I got a date.”

“You do? Who’s the lucky lady?”

Of course, Dean could have gone with it and not tell Sam about Castiel, but what would have been the point of that? A challenge was a challenge, there was no point in shying from it.

“Not a lucky lady, Sammy. A lucky dude!”

This time, Sam stopped watching his show to look him in the eye. “A dude? You were serious with that challenge crap?” He paused, now looking confused. “Didn’t you say you would turn him down when he’d ask you out? If that’s the case, then why—”

“It didn’t go as planned, all right? But everything’s cool, I’m still gonna shut this thing down, just a bit later in time.”

“When? After he’s fucked you into the mattress? Are you gonna turn him down then?”

“Sammy!” Dean was right about to choke. “There’s no fucking anyone in no mattress. None whatsoever. And even if there was – and there won’t be – I wouldn’t be the one on the receiving end. Got it?”

“Whatever you say, man… that whole thing is just too fucked up, even for you.”

Deep down, Dean knew that, but he was too invested now. So he just shrugged, looking at his shoes. Soon, Sam was back watching his show, and Dean still didn’t know if he would have the apartment to himself. Which meant he had to ask again. He sighed.

“So? Can I have the apartment or not?”

“I’m tempted to say no, but I don’t want any part of this. So yeah, you go be a douche to that guy. See how well you can live with yourself after that.”

“You see how well you live with yourself,” Dean replied under his breath, not waiting for a comeback before going back to his room.

He had an outfit to plan. And a date.

~ • ~

Dean spent his whole day in a nervous state. He even spent his lunch hour in his office, not wanting to risk crossing paths with Castiel. He didn’t want to see him before they were to meet in the parking lot.

The half-hour leading to five o’clock had to be the longest Dean has ever had to live through. He spent it with his eyes on the clock, getting startled when his phone rang at 4:48.

“Dean Winchester,” he answered, still with his eyes on the clock.

“Hello, Dean. It’s Castiel.”

Dean’s gaze shifted to the phone. Was Castiel calling to cancel? If he was, did that mean that Dean was getting rejected? Losing?

“Are you still there?”

“What? Yeah, sorry. Hi, Cas.”

“Oh, we’re already at the nickname stage, are we? I guess that means we’re still on?”

“Yeah?”

“Great… I just thought I’d make sure. Since I haven’t seen you since that other day.”

“No… yeah… we’re still… yeah.”

“Parking lot at five, then. See you soon.”

The line went dead with Dean still holding the phone to his ear. He hung up, looking back at the clock again. Ten minutes to go, and then he’d be meeting a dude in the parking lot. For a date. They’d go grab some food, and then they’d come back to his place, and…

He took his cell phone, itching to call Charlie. She had always been the best person to talk to when he didn’t know what to do. Except he knew she would never help him with this. He put the phone back down, now tempted to call Castiel and tell him something came up. That he had an emergency to tend to. That would be okay, right? That would mean that he was the one doing the rejection, so he would win.

Right?

For some reason, he found himself never calling him back and making his way out at five. Castiel was already there, waiting for him a little further into the parking lot. Dean took a deep breath as he walked toward him, still thinking that he could shut this down now. He didn’t.

“Hey, stranger,” he said, stopping a few paces before getting too close. Castiel smiled as he closed the distance between them, once more kissing his cheek.

“Hello, Dean.”

Dean felt his face warm up when he saw Kali looking at them. Her smile was a little too wide, and she wiggled her fingers at them. Dean cleared his throat, waving back at her.

“So… can we get out of here?” he said, worried about what his coworkers might say or think.

“I don’t know if you had anything planned already, but I was thinking we could go the groceries together. In the mood for anything in particular?”

“I make a mean burger,” Dean said. He internally winced when Castiel’s nose scrunched up a bit. Kali said it: Castiel was a cultured dude. He seemed to notice Dean’s unease and let out a soft chuckle.

“Don’t get me wrong, I love me a good burger,” he said. “I just think we should go for something a little more… hmm… special?”

“What? Like some kind of fancy salad?”

This time, Castiel threw his head back, laughing. “Unless that’s what you want, I think I’d rather go for pasta. I know this little grocery store not too far from here. They make their own bolognese, and it’s delicious. Fresh pasta, parmesan, garlic bread…” He tilted his head again, smiling. “Maybe not garlic bread. I mean… it does leave a strong aftertaste in the mouth.”

When Castiel licked his lips, Dean’s gaze automatically dropped to them. His face warmed up again when he realized what he was doing, and what Castiel actually meant about the bread. “Yeah… maybe no garlic bread,” he said in a stammer. Not that he intended on kissing the guy, but he couldn’t let him know that. Not yet.

Castiel nodded, and if the creases around his eyes were anything to go by, he really liked where this evening seemed to be going. The way he lightly brushed Dean’s hand as he followed him to his car was another clue of that fact.

If such a light touch was enough to elicit shivers down Dean’s spine, it was nobody else’s business but his. The sooner this evening would be done with, the better.

~ • ~

As he had promised, Sam had vacated the apartment. Dean let out a relieved breath when he opened the door to let Castiel in.

“Welcome to Casa di Winchester,” he said with a flourish of his hand as he led the way to the open kitchen. They dropped their bags on the island, Castiel standing close enough to Dean that their shoulders were touching.

The only way Dean found to move away was to start pulling items from the bags and setting them around the kitchen; the sauce and pasta near the stove, the fancy ice cream dessert – Castiel said it was called Tartufo – in the freezer, and the baguette and parmesan cheese on the table.

“I forgot to ask, but you have a corkscrew, right?” Castiel asked as he pulled the bottle of wine from the bag. “We could manage if—”

“What self-respecting adult doesn’t have a corkscrew?” Dean said in a huff as he opened a drawer. He had to look for it, but he did find the bottle opener his brother had bought the year before. Not that he intended on telling Cas that.

“Thanks,” he said. “You don’t mind if I open this now, do you? I love to prepare dinner with a glass in hand.”

“I don’t mind, but I thought I’d be the one preparing dinner…”

Dean pulled two stemmed glasses from one of the overhead cupboards, giving them a discreet brush to get rid of the dust. That was another thing Sam had been adamant they needed, even if neither of them ever drank wine.

“Fine. I love to have a glass of wine in hand while I watch handsome men make me dinner.”

Dean huffed, embarrassed by the compliment but also feeling kind of validated. Kali could suck it. Romeo Novak over there thought he was handsome.

It didn’t take long to prepare dinner, seeing as everything was pre-made. Even the appetizers – a plate of weird stuff Castiel called antipasto – was something he had bought already made. They slowly munched on that while the sauce and pasta warmed up, Dean having to admit that the salty salami-like meats, fancy cheeses, and pickled veggies weren’t all that bad.

“I could get used to this,” he said after swallowing down a delicious mix of soft cheese and spicy olives. “Do you eat like that all the time?”

Castiel took the time to suck the oil and vinegar from his fingers before answering. “No, of course not. This is more like a treat. You know, good company…” He raised his glass to tip it toward Dean. “Good wine. Good food. When you abuse the good things, what’s left to look forward to? Am I right?” He winked before sipping on his wine, sending Dean a heated gaze over the rim of his glass.

“I wouldn’t know… I pretty much take what I want when I want it. You know; Good food, good booze, good sex. I really think you should live your best life while you can, you know?”

Castiel gave him a small nod. “You didn’t have an easy home life, did you?” he said after some time, making Dean almost choke on his wine.

He braced himself, his usual walls starting to come back up. “What makes you say that?” He mentally patted himself in the back that his voice came out sounding normal.

“I don’t know. I could be wrong. It’s just a feeling, really. I didn’t want to offend you.”

“You didn’t offend me,” Dean said, even though he didn’t really want to get into the shit show that had been his childhood. Thankfully, the timer on the stove beeped, alerting them the pasta and the sauce were ready.

He turned away to take care of dinner, straining the pasta, dividing it all into two plates and pouring the sauce over them. When he turned with the plates in hand to bring them to the table, he saw Castiel had moved everything to the living room.

“I hope you don’t mind… your couch just looked so comfortable. And we can start watching that movie you were telling me about.”

Since there were no real reasons for Dean to refuse, he shrugged and joined Castiel on the couch, gently putting the plates down on the glass table.

“It smells delicious,” Castiel said after smelling the dish. As if he hadn’t been the one choosing the food.

“It does,” Dean agreed, already tearing off a piece of baguette to dip it in the sauce. He was munching on the second half of his bread when he noticed Castiel had yet to touch his plate. “You’re not hungry?” he said around his mouthful.

“I’m sorry… I kind of zoned out, there. Your eating habits are mesmerizing.”

Dean swallowed, clearing his throat before speaking again. “Sammy says I’m a pig…”

“Well, I think it’s adorable.”

Dean once more felt his face grow warm while Castiel worked on twirling a nest of noodles on his fork. It was Dean’s turn to be mesmerized, unable to look away as Castiel licked his lips, parted them, then closed them on the fork and pulled it out.

He let out a pleased hum, and Dean needed to clear his throat once more. At least, it helped shake him out of his daze as he got interested in his plate again. Except Castiel had other plans.

“So? Want to start up that movie? What was it? The Defenders?”

Dean’s urge to roll his eyes was strong, but he resisted. “ _The Avengers_ , man. How do you not know that? I can get that you wouldn’t have seen it, but that you haven’t even heard of it? Have you been living under a rock?”

“Of course, I haven’t. I don’t own a television.”

“You’ve got a computer, don’t you? You don’t go to the movies?”

“I do… I just haven’t stumbled upon that one, I guess. So it’s about these superheroes, right? I haven’t seen much of this type of movies. I won’t lie, I think it sounds a bit… vapid and childish.”

If Dean didn’t have a bet to win, he’d be kicking this guy right out of his apartment. How dare he call the _Avengers_ vapid? Or even childish? That guy was a real prick! Turning him down once he’d be all hot and bothered would be the best feeling in the world.

“Look, if you’d rather watch something else, I wouldn’t mind,” Dean said, his tone overly sweet. “I’ve seen it already.”

“But you like it.”

Dean smiled as he wrapped a hand over Castiel’s knee. “I won’t be enjoying myself if the movie bores you to death. What kind of movies do you like to watch?”

Instead of answering, Castiel wrapped his own hand over Dean’s after wiping his mouth with a paper napkin. “We don’t have to watch a movie, you know. We could just… talk?” He leaned forward, his eyes locked with Dean’s. “Or not.”

When Castiel’s lips landed on his, it was like a short-circuit in Dean’s brain. While a part of him was cheering and ready to finally end the whole date, there was this other part really getting into it.

Castiel was the one that pulled back, making sure to catch Dean’s gaze. He didn’t say a word, but the question in his eyes was clear as day: Is this all right? Dean’s response came by him leaning forward to catch Castiel’s lips again, ever so softly.

The kiss was chaste, but Dean didn’t mind, mostly because it would be easier to break things off if neither of them had the mind to go any further. Castiel might have read his mind because the next second, he brushed the seam of Dean’s lips with his tongue. Dean’s eyes, which he had kept open because it wasn’t that kind of kiss, fluttered close.

~ • ~

“You kissed him? With tongue?”

Dean had known Charlie for years, and never did he hear her voice reach these notes. When outraged, she could easily rival Mariah Carey’s whistle tone.

“It’s just a kiss, Charlie. Means nothing.”

“What happened next?” Jo asked.

Dean’s form straightened. He grinned, holding a hand up. “I pulled back, and then I said ‘I’m sorry, you’re a really nice guy, but I don’t think we work. I was mistaken, I don’t have a single gay bone in my body.’”

“Liar.”

Dean scoffed, turning to face his brother. “Not a liar, Sammy. I did what I said I would do. We were kissing, and then I let him down gently.” He chuckled, rubbing at his chin. “Kissing a guy is different, though… right? All that stubble… I swear, my chin was angry red afterward.”

Jo squinted at him. “Angry red, Dean? Your chin was all chaffed after just one little kiss?”

~ • ~

_It didn’t take long for Dean to have a lap full of Castiel, their fancy pasta dinner going cold on the coffee table. Dean’s ideas of shutting things down had already been forgotten, the blood having left his brain to pool in his groin._

_“God, you’re hot,” Castiel said. He had both hands cradling Dean’s face, his blue eyes boring holes in Dean’s green ones. “If I’d known you were bi…” He didn’t get to finish his thought, Dean leaning in to capture his mouth again._

_They kissed for what felt like a long time. Up until clothes started coming off. It was Dean who instigated the disrobing, needing to feel Castiel’s warm skin brushing against his. How a naked male torso crushed against his felt this good, Dean couldn’t explain. He always believed he was a boob man, and right now, he didn’t miss them one bit. It was when he dipped his hands low in the back of Castiel’s pants that he started to think that he may be an ass man, after all._

~ • ~

“Totally makes sense,” Sam said, just as squinty. “You’re a pervert, Dean. I know you, and there’s no way you didn’t take advantage of a willing pair of lips. And if your chin got—”

“Dude lips, Sam. How many times do I have to tell you all that I’m not into guys?”

“You fell for him, didn’t you?” Charlie said, looking far too smug. “He kissed you, and you loved it, and you guys made out a whole lot, didn’t you?”

Having friends might have been one of Dean’s favorite things, he still hated how well they knew him. He huffed and rolled his eyes. “All right… maybe there was more than one kiss.”

“Really, Dean? How many kisses were there, huh?”

“I don’t know, Charlie… who cares?”

“I care!”

“Fine… I can’t tell you how many kisses there were, okay? Who counts kisses anyway? That would be creepy as fuck!”

It was Jo who said it first. “You slept with him. You totally had sex with a dude, dude.”

“No, I didn’t.” Dean knew his face was crimson red by now, yet he couldn’t find the will to tell the truth. He had sex with a dude, and it was awesome, and Castiel was awesome, and—

~ • ~

_Dean could have stayed there for the rest of eternity, but Castiel had other plans in mind._

_“This is a very nice couch. It’d be a pity to stain it,” he said, leaning backward to catch Dean’s gaze again. “What do you say we move this to the bedroom?”_

_There was an alarm bell somewhere in the back in Dean’s brain, but it was quickly drowning in lust. His own, and the one he could see crowding Castiel’s pupils. He gave him a feeble nod, almost whining at the loss of Castiel’s weight on him._

_He may have been the one leading them to his room, Dean still felt like he had no control over what was happening. He didn’t have control over his own desires either as all those new sensations and desires roamed under his skin._

_He wanted Castiel like he hadn’t wanted anybody in a long time, if ever. It was exciting, it was new, and it made it all the sexier. The only thing that didn’t change was how easy it was to manhandle him into the bedroom. Women did it, and Castiel was no different. Before long, Dean was pushed backward on his bed with Castiel crawling over him._

_“I’m what they call a power bottom,” he said, lavishing Dean’s chest with kisses between every word. He wrapped his mouth around a nipple to suck and bite on it, making Dean cry out. “D’you have a problem with that?”_

_Dean could only shake his head vigorously. Castiel gave him a crooked smile and went back to kiss down his torso, lapping at his navel as he started undoing Dean’s pants._

~ • ~

“He totally did!” Sam said. Or exclaimed, rather. “He’s got that same look he had when I found his pink panties in the wash, and—”

“Sammy, shut your big fat mouth, would you? Those weren’t mine okay? They were Rhonda’s.”

Sam chuckled. “I remember Rhonda, and she was a tiny girl. There’s no way those were hers. They looked more like your size, Dean.”

The girls had started giggling, and Dean was increasingly convinced that he could have fried an egg on his own face. He growled, promising himself he’d get Sam back for that. Just, not right now.

“All right, fine! I might have slept with Castiel a little bit.”

“How do you sleep with someone a little bit, Dean? Either you did, or you didn’t.”

~ • ~

_With Castiel’s amazing mouth wrapped around his shaft, Dean was lucky even to be able to think. Not that his thoughts had any kind of substance, but he didn’t care. All he could concentrate on were the mouth on him, and how soft the Castiel’s hair felt in his fingers._

_Just like the firm pecs, Dean found himself not minding the low grunts and hums Castiel would let out as he sucked him off. Just like this new feeling of stubble brushing against his thighs, he relished in it._

_“Cas…” he soon moaned, opening his eyes to look downward. The shock of those blue eyes looking up at him almost made him come right then and there. Castiel let him go with a pop, the sight of his mouth and chin slick with spit making Dean’s heart skip a beat._

_“Dean…” Castiel answered under his breath as he climbed back up to ravage Dean’s mouth. He let him go too quickly, settling on his lap. “How do you feel about eating ass?”_

_“I—hmmm—I don’t—”_

_“Don’t worry, sweetheart. Daddy’s got you,” Castiel said, and it was almost enough for Dean to grow cold. He may have been willing to experiment in bed, he was pretty sure he didn’t have a daddy kink._

_“No dad stuff,” he said in a stutter, worried it would make things awkward. But Castiel smiled back at him._

_“Roger that…” Castiel said, dipping down to kiss him some more. “Good thing I came prepared,” he added as he got up on the bed, his feet on either side of Dean, and started undoing his pants._

_Dean licked his lips as his eyes zoned in on Castiel’s crotch. He couldn’t look away as Castiel worked on his pants, Dean’s fingers tingling he was so eager to touch. Soon, Castiel only had a pair of oversized white boxers on, and Dean could have laughed at the sight if he hadn’t been so horny._

_Two thoughts bounced around in Dean’s brain when the boxers dropped: Castiel’s dick was fucking big, and thank God he wouldn’t be the one getting rammed in the ass._

_Castiel was still standing over him, fully naked now, and Dean couldn’t look away. He held a hand out, eager to touch, needing to pull him back down. Castiel gave him a small headshake, and he smirked before turning around._

_Dean now had a beautiful view of Castiel’s butt. It was a nice butt, and it looked firm, and— He almost choked on his own tongue when Castiel sat down on him. His spread buttcheeks gave Dean an unobstructed view of the buttplug snug in his hole._

_“Oh, shit…”_

_“You like?” Castiel asked, wiggling his ass a little._

_There was nothing Dean could think to answer, so he let his hands speak instead. He grabbed the meat of Castiel’s cheeks, spreading them a little more. His mouth watered as he pushed the plug softly with his thumb and Castiel sucked in a breath._

_“Got lube?” Castiel asked, sounding wrecked. Dean’s brain came to a stop. He didn’t have lube, because it wasn’t something he usually needed. Not with girls, and not on his own either. And he certainly hadn’t planned on actually having sex tonight._

_“No…”_

_Castiel looked at him over his shoulder, a single brow quirked high. “You don’t? Did you think we weren’t gonna fuck tonight?”_

_“I—I didn’t want to assume—I didn’t know.”_

_“Wow. Didn’t think I’d ever meet such a gentleman,” Castiel said as he got off the bed. Dean’s heart sank, convinced the night had come to an end. “Be glad I’m not a gentleman,” Castiel said as he rummaged through his discarded pants. He soon showed Dean a small packet of lube._

_“Oh, thank God!” he said, making Castiel chuckle._

_The next second, Castiel was back on his lap, facing him this time. “Did Little Dean get scared?” he asked before taking him in his now lubed hand. “He’s gotta be big and strong for me. Think you can muster that?”_

_As he spoke, Castiel kept stroking Dean’s dick, coating it with lube and making Dean’s insides catch on fire._

_“If you don’t get on it soon, you ain’t gonna be riding me for long, man.”_

_Castiel let him go and smiled. “It won’t last long anyway, Dean. You know how this goes.” He leaned forward to speak against Dean’s cheek while he took the plug out. “You’re gonna have to fuck me more than once, baby.”_

_Before Dean could object – not that he would – Castiel grabbed his dick at the base and moved to brush the tip against his hole. The next second, Castiel was pushing himself down on him, taking his time to take him all in, right down to the hilt._

_“How’s that?” Castiel asked, his voice tight._

_“Aah—awesome—God—so hot…”_

_“Saddle up, cowboy,” Castiel said, already out of breath, before moving his hips up to slam them back down._

_Whatever happened next, Dean didn’t see or hear anything other than Castiel. There could have been a volcano erupting outside his window that he wouldn’t have known it. Right now, his world is Castiel, and Castiel’s body, and his ass, and the dick slapping his belly._

_When Dean grabbed it, Castiel’s dick, it was mostly to stop it from bouncing around. It was all it took for Castiel’s moans to get louder and Dean caught on. He looked up, once more locking eyes with Castiel, then started stroking him._

_It was different, having a dick in his hand other than his own. And the angle was weird, too, but he couldn’t find it in himself to care. Castiel loved it, and he was a mess, as was Dean and, as Castiel predicted, it ended all too soon._

_The second and third times were much better._

~ • ~

Charlie wasn’t laughing anymore. “I can’t believe you did this, Dean.”

“Don’t gimme that speech, would you? You have a different girlfriend every other week, so I don’t think you can point fingers at anyone, all right?”

“Maybe I get around, but at least the girls I get with know what’s up. You, you just went and seduced some poor guy, and now you won’t be calling him back?”

“But it’s okay if I do it to girls?”

At this point, Sam and Jo had kind of deserted the living room to hang by the kitchen island. When Dean and Charlie got into those types of heated arguments, nobody was safe.

“Of course, it’s not okay. When did you ever hear me congratulate you for being a douche?”

“They’re not calling me back either, so you know… we’re all douches, guys and girls alike. Can’t tell you the last time a girl has really been interested in me. All they want is a good dickin’, and then it’s adios. We go our separate ways, and everyone’s happy.”

“Except that’s not what you did to Castiel. You made him believe you liked him. Hell, you even went all the way with him just to prove a stupid point. Just so Kali would give you the time of day. And that’s an awful thing to do.”

“You’re a girl, you don’t get it, okay? Guys are not like that. I’m sure he knows it was a one-time thing. No pining, on either side. We’re cool.”

“So you told him as much, then?”

“I swear, Charlie. There’s no need. He’s a guy, he gets it.”


	2. THE REAL ENDING (NOT HAPPY)

The next Monday, Dean was a little too eager to get to work. Maybe because he didn’t party much that weekend, which could be explained by Charlie being pissed at him.

He went to drop his coat and bag in his office, but before he could make his way to the kitchenette, Kali came to find him, two coffee cups in hand. She offered him one, a knowing smile on her lips.

“So I hear someone had a nice date on Friday? Wine, fancy Italian food, never getting to watch a movie before taking things to the bedroom?” She gave Dean a once over, her gaze staying on his butt a little too long. “I shouldn’t be surprised, I mean… you are pretty.”

“Calm down, Kali. Just wanted to prove to you that I wasn’t out of Castiel’s league. Who’s laughing now?” He decided not to ask how she knew everything, somewhat flattered by the fact that Castiel might have gloated about getting with him.

She took a step forward, placing a flat hand over his heart. “You did all this for me?” she asked, to which Dean nodded. “So let me get this straight – no pun intended. You went on a date with a guy, wined and dined him, then had sex with him just to prove me wrong?”

“Well… kinda?”

Kali stepped back, the look on her face now a pitying one. She shook her head and clucked her tongue. “I think this has to be the saddest thing I’ve ever heard. I mean, I get how some people can be in denial over their own sexuality, but you, you take the cake.”

“What?” Dean could feel the colors slowly draining from his face.

“It’s fine if you’re gay, Dean.”

“I’m not gay.”

“Fine, bisexual, who cares? I mean, I’m glad you’re finally figuring things out for yourself, but please don’t use me as an excuse.”

Panic was starting to settle deep in Dean’s belly. “No, Kali, you don’t get it! What I really want is to f—hmmm—what I really want is to date you. I just thought that if you saw that I could get a guy like Castiel, then you’d realize I was good enough for you.”

“What are you? Twelve?” She came back in, this time to grab his face with one hand and squeeze his cheeks together. “I don’t fucking care if Novak fancies you or not, Dean. The fact of the matter is I don’t date children. Do you hear what I’m telling you?”

Since he couldn’t really respond, he just gave her back an energetic nod. She nodded back at him, letting his face go before gently tapping him on the cheek.

“That’s a good boy,” she said as she left his office.

Dean glanced at the clock, wondering if he’d have time to swerve by Castiel’s own office before the board meeting was to start. He didn’t need to go very far, spotting him standing by the water cooler. He was chatting with Balthazar, one of the execs.

He had started making his way to them when he noticed Balthazar brushing a soft hand on Castiel’s arm before leaving. Dean straightened his stance, walking faster now. What the hell? Was that douche coming on to Cas?

“Hey,” Dean said, crowding Castiel’s space. “Fancy seeing you here.” He smiled, tempted to dip and kiss him, but he didn’t. Maybe they could find somewhere a little more intimate later. Have lunch in Dean’s office, perhaps.

“Hello, Dean,” Castiel said, again with that soft smile on his lips. Damn, that was a tempting mouth. “I had fun on Friday,” he said. His voice was quiet, but he still took a step back, taking his warmth away from Dean.

Rocking on his heels, Dean resisted the urge to get closer again as he answered. “Yeah… was fun.”

There was a long pause, Dean searching for something else to say. He kind of knew what he wanted to say, but he could have sworn the air between them had grown colder. Cold enough for doubt to creep in the back of Dean’s mind. Was Castiel lying? Did he not have a good time?

“So—” he started to say, right when Castiel said, “See you around.” and started walking away.

“Yeah, see you—whoa—what?” Dean closed the distance between them, pulling on Castiel’s shoulder so he would turn around. “That’s it? See you around?” he said in a hiss, still mindful of their surroundings.

Castiel did that thing Dean didn’t find cute at all; Scrunching his brows and tilting his head. “Well… we do work together. We are bound to cross paths once in a while.” His expression then morphed into one of understanding. “Oh, because of what happened between us?”

“Well… duh? Thought we had a good time.”

Castiel was smiling now. “Of course, we did. I had a great time.” He discreetly put a hand under Dean’s jacket to rest it on his hip. “You’re very cute and eager…” He moved away, just enough to be able to look him up and down. “And you’re really sexy. But we both know this was a one-time thing, Dean.”

Shit!

“Yeah, no, of course, I know that,” Dean said, working hard not to sound too surprised. Even though he totally was. He must have done something wrong. Getting dumped by a dude, by Novak, wasn’t something he wanted to consider. “I mean… we could do it again,” he said, brushing imaginary dust from Castiel’s lapel. “Doesn’t have to be on a Friday… most of my weeknights are free. I mean, whenever… whatever...”

Dean knew he was starting to sound pretty desperate, but Castiel had said it: He had a great time, so there was no way he was gonna pass up the opportunity to see him again, right? He was Dean Fucking Winchester!

Castiel moved his hand to cradle his jaw, ever so softly. “You’re adorable, but I think we’d better keep things simple, Dean.” He let his face go and moved away, right when Balthazar came back from the kitchenette.

The blond exec gave Castiel a cup of coffee before wrapping an arm around his shoulders. He smirked as he gave Dean a lazy once over. “Mr. Winchester,” he said, his tone dripping with contempt.

“Balthazar.” Dean couldn’t have cared less about conventions right about now. He had never liked him, and seeing him being all over Castiel certainly wasn’t helping. “Wassup?”

“Pleasure, as always,” Balthazar just said before turning to Castiel. “Ready to go to work? Can’t wait for this day to be over and then we can…”

Whatever he ended up saying, Dean didn’t hear it. Balthazar was steering Castiel away, and he barely had time to wave Dean goodbye. Not that he seemed to mind, clearly under Balthazar’s spell as they walked away.

Standing alone by the water cooler, Dean tried to make sense of what had just happened. He had been rejected. By a dude. And it hurt like hell. Not only because being rejected sucked, but because Dean had really thought something special had happened. Except that something apparently had been one-sided.

Oh well…

**Notes for the Chapter:**

> I honestly don't know how to end this ending... it's a testament as to how much I don't like it! lol
> 
> I mean, it was fine in the show, it was a one shot and I don't think there's ever anything said about it ever again. The character ("played" by Dean here) goes back to being a womanizer and that's all there is to it.
> 
> Which is why I had to write another ending... one that's more to my liking. We're talking about Castiel and Dean here, of course I want them to end up together!!!
> 
> So if that's also what you want, just go to the next chapter! :D (the real ending, as far as I'm concerned)


	3. MY ENDING (HAPPY)

The next Monday, Dean was a little too eager to get to work. Maybe because he didn’t party much that weekend, which could be explained by Charlie being pissed at him.

He went to drop his coat and bag in his office, but before he could make his way to the kitchenette, Kali came to find him, two coffee cups in hand. She offered him one, a knowing smile on her lips.

“So I hear someone had a nice date on Friday? Wine, fancy Italian food, never getting to watch a movie before taking things to the bedroom?” She gave Dean a once over, her gaze staying on his butt a little too long. “I shouldn’t be surprised, I mean… you are pretty.”

“Calm down, Kali. Just wanted to prove to you that I wasn’t out of Castiel’s league. Who’s laughing now?” He decided not to ask how she knew everything, somewhat flattered by the fact that Castiel might have gloated about getting with him.

She took a step forward, placing a flat hand over his heart. “You did all this for me?” she asked, to which Dean nodded. “So let me get this straight – no pun intended. You went on a date with a guy, wined and dined him, then had sex with him just to prove me wrong?”

“Well… kinda?”

Kali stepped back, the look on her face now a pitying one. She shook her head and clucked her tongue. “I think this has to be the saddest thing I’ve ever heard. I mean, I get how some people can be in denial over their own sexuality, but you, you take the cake.”

“What?” Dean could feel the colors slowly draining from his face.

“It’s fine if you’re gay, Dean.”

“I’m not gay.”

“Fine, bisexual, who cares? I mean, I’m glad you’re finally figuring things out for yourself, but please don’t use me as an excuse.”

Panic was starting to settle deep in Dean’s belly. “No, Kali, you don’t get it! What I really want is to f—hmmm—what I really want is to date you. I just thought that if you saw that I could get a guy like Castiel, then you’d realize I was good enough for you.”

“What are you? Twelve?” She came back in, this time to grab his face with one hand and squeeze his cheeks together. “I don’t fucking care if Novak fancies you or not, Dean. The fact of the matter is I don’t date children. Do you hear what I’m telling you?”

Since he couldn’t really respond, he just gave her back an energetic nod. She nodded back at him, letting his face go before gently tapping him on the cheek.

“That’s a good boy,” she said as she left his office.

Dean glanced at the clock, wondering if he’d have time to swerve by Castiel’s own office before the board meeting was to start. He didn’t need to go very far, spotting him standing by the water cooler. He was chatting with Balthazar, one of the execs.

He had started making his way to them when he noticed Balthazar brushing a soft hand on Castiel’s arm before leaving. Dean straightened his stance, walking faster now. What the hell? Was that douche coming on to Cas?

“Hey,” Dean said, crowding Castiel’s space. “Fancy seeing you here.” He smiled, tempted to dip and kiss him, but he didn’t. Maybe they could find somewhere a little more intimate later. Have lunch in Dean’s office, perhaps.

“Hello, Dean,” Castiel said, again with that soft smile on his lips. Damn, that was a tempting mouth. “I had fun on Friday,” he said. His voice was quiet, but he still took a step back, taking his warmth away from Dean.

Rocking on his heels, Dean resisted the urge to get closer again as he answered. “Yeah… was fun.”

There was a long pause, Dean searching for something else to say. He kind of knew what he wanted to say, but he could have sworn the air between them had grown colder. Cold enough for doubt to creep in the back of Dean’s mind. Was Castiel lying? Did he not have a good time?

“So—” he started to say, right when Castiel said, “I’d like to see you again.” Dean’s heart seized in his chest.

“Yeah—whoa—hmmm—I mean…” Dean closed the distance between them, close enough to share warmth but not enough to touch. It may have been unexpected, it still felt like it was all Dean had been waiting for. “I think I’d like that,” he said, his voice shaky. He was turning to mush right then and there. “I just though…”

“What? You thought I had a habit of going to bed with anyone who dared to look my way?” If Castiel hadn’t sounded highly amused, Dean could have thought he had insulted him.

“No… I mean… you’re a guy, and—”

“I take it that, as a guy, you’re a regular one-nighter?”

Dean swallowed. If Castiel had been a girl, even Kali, he knew he might not have been so eager to see him again. He decided not to think about that right then and there, discreetly brushing Castiel’s hand with the pad of his fingers. “Not on purpose,” he said, not wanting to get into that either.

“Should I be flattered?”

The lump growing in Dean’s throat prevented him from answering, so he shrugged instead, his gaze a pleading one. 

“I see… What do you say we have dinner together tonight? For real this time, taking the time to fill our bellies. Let’s go to my place, have actual dinner and chat. I’m thinking you might have a lot on your mind right now.”

Castiel smiled and leaned in to kiss his cheek, right there in the middle of the office, and Dean didn’t care one bit. With the lips warm on his skin, he glanced to see Kali looking at them with that eternal smirk on her lips.

She raised her cup and gave him a tiny bow as if accepting that maybe, Dean wasn’t out of Castiel’s league after all.

Not that he could find himself to care anymore.

**Notes for the Chapter:**

> I know... this ending isn't all that good either. I'm aware of that. I honestly think the story itself was more interesting. Hey, there was a bit of smut so... you know. Not a total waste of time, right?
> 
> I just had to let it out, been bugging me for far too long. Now I can concentrate on other stuff, dang it!
> 
> I hope you still had some fun reading this. All I can say is that's the start to a beautiful adventure for our boys. Because I said so... I eventually came to the conclusion that Dean (in that piece) is probably homoromantic (and bisexual)... it could be an explanation, right?
> 
> So yeah! This was me destroying not one, but two bouts of TV that should never even have met in the first place. No need to thank me, it was my pleasure!


End file.
